


A Fine Memory

by jackles67



Series: The Skirt Thing [2]
Category: Supernatural
Genre: Crossdressing, M/M
Language: English
Status: Completed
Published: 2013-06-29
Updated: 2013-06-29
Packaged: 2017-12-16 13:14:28
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 2,314
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/862415
Author URL: https://archiveofourown.org/users/jackles67/pseuds/jackles67
Summary: <blockquote class="userstuff">
              <p>Dean follows through on his promise to buy Sam some panties</p>
            </blockquote>





	A Fine Memory

**Author's Note:**

> Unbetaed

Once Dean’s in the store, he pictures every pair he looks at on Sam and it’s hard not to buy everything, just spend the wad of hard-earned cash in his pocket on black lacy things that’ll go halfway up Sam’s ass, soft white cotton that Dean wants to make Sam wear in the shower so they turn transparent, dark red silky thongs that’ll fail delightfully at keeping everything tucked away.

He settles on a pink, satin pair, a basic cut with a tiny bit of lace trim and a little bow at the front. He gets the black lacy ones too, figures he’ll save them for another time - springing new panties on Sam just sounds like a good time. Dean buys Sam a new skirt, too - pale pink, nearly white, with a floral lace pattern. It sits high on the mannequin’s waist, barely skims tops of her thighs - Dean’s pretty sure Sam will love it.

Dean knows he could just shove the panties into Sam’s hand when they stop for gas or pass them under the table for him to slip on in a diner bathroom, but he wants them to take their  time, to make it good, so he waits.

Now that Dean’s trying to get Sam alone though, it seems practically impossible. They’re on the move, following something from town to town and the only time Dad leaves them alone is when Dean’s driving Sam in the Impala, following behind Dad’s truck.

Dad takes off a little earlier one morning and Dean waits for Sam, sleepy and grouchy, to shower so they can check out of this motel and get on the road. Dean leaves to get coffee and comes back to find Sam already sitting in the car, wrapped in one of their big blankets, head resting against the window, eyes closed. Kid’s probably already passed back out, so Dean grabs his duffel and loads up the car, drops the coffee into the cup holder and starts the car.

Dean realizes Sam’s not sleeping after a couple minutes - his breathing’s wrong, the set of his shoulders is too tense. Dean’s about to ask what’s up when something catches his eye - a slip of pink lace visible between the folds of the blanket. Oh.

Sam must’ve found the skirt - which means he found the pink panties, because Dean had them wrapped together and ready to hand to Sam the second he found a good time - and he... put it on.

And now he’s pretending to be asleep. Dean’s caught somewhere between exasperated and blindingly turned on.

Dean shifts in his seat, cock hardening in his jeans. A few inches of fabric has him getting so hard he’s thinking about unzipping on the fucking highway. Jesus. He has to see the rest, has to see what Sam’s wearing with it, what it looks like when Sam gets hard under that pretty pink lace, if he put on the panties as well.

He flicks the blanket back in one quick move, holds it back when Sam jerks and reflexively tries to cover himself.

Sam’s legs are bare, all the way down to his sneakers - Converse, and somehow the fact that he’s wearing his normal shoes with that fucking skirt has Dean nearly swerving off the perfectly straight road. Sam’s knees are just barely spread, the skirt falling gracefully over the seat, barely covering the obvious bulge. He’s wearing Dean’s Metallica shirt with it, faded black fabric soft and worn, completely contrasting with the delicate floral lace.

Sam stops trying to tug the blanket back, letting it fall away and turning to face Dean, blushing but defiant.

“I ran out of clean shirts.”

Dean nods absently, trying very hard to glance at the road every once in a while. Why did Sam put it on now, when they’re supposed to be driving for five hours straight? That line of thinking just leads to picturing Sam finding the skirt and immediately trying it on, eager and excited and so fucking hot.

Dean throws on some Led Zeppelin to try and get his mind off the hot pulse between his legs, thrum of arousal tugging every ounce of his attention away from the road to the passenger seat. This isn’t the time.

“Is it - is this okay?” Sam asks, uncertainty creeping into his voice. God, Dean just really wants to be able to look at him like he deserves right now, instead of the quick glances he's throwing at him between turns as the road grows more curvy with every mile.

“Sure. Got it for you.” Dean reaches a hand over, pats Sam’s leg comfortingly and leaves it there, thumb brushing over Sam’s warm skin, fingertips curling around to the soft inner part of his thigh. He knows it was a mistake the second he feels Sam shift, his legs parting a fraction of an inch more. Fuck, there’s no way he’s going to be able to drive like this, with Sam so willing under his hand.

Dean slides his hand up, slow as he can, pulling towards him so Sam has to open wider, spreading his thighs for Dean. It’s a struggle, but Dean makes himself drag his hand back down to Sam’s knee before bringing it slowly back up to push under the hem of the skirt, stopping just shy of the top.

Sam slides down the seat, skirt riding up as he moves into Dean’s touch until Dean finds himself cupping Sam’s satin-covered cock, fabric stretched tight, so thin Dean can feel every detail. He runs his fingertips over the panties lightly, feels Sam shiver under the touch and does it again, this time all the way up over the growing damp patch at the head.

Dean keeps his fingers light, plays over Sam’s cock like a tease until Sam is whining, hips coming up to push his cock into Dean’s hand, trying to get some real friction. When Dean chances a glance over, Sam’s leaning back, legs spread and skirt pushed up over his hips, pink panties on display, every line and curve of his cock clear through the soft fabric. God, he’s fucking perfect like this.

It’s almost too hard to tear his gaze away and the Impala drifts off the road for a second, just an instant of gravel instead of paved road but the sound is enough for Dean to drag his hand away and force himself to keep driving.

Sam whines at the loss of contact and brings his own hand down to his cock but Dean grabs his wrist, holds him still.

“Don’t.” It comes out ragged and Sam shudders but doesn’t resist, just obediently drops his hand back to his side. Dean reaches over and tugs Sam’s skirt back down to cover him, the soft friction of fabric on fabric sending another shiver through him. Jesus, he must be really fucking sensitive right now.

“Dean, I can’t -” Sam cuts himself off, bites his lip and turns his head away.

Dean takes the first tiny dirt road he sees, parks and turns to watch Sam as the engine cuts out.

“Why now?” God, why is he even talking when he could be touching Sam, could be making Sam come in his pretty pink panties.

“I couldn’t wait. Saw the skirt and -” Sam shrugs, blush spreading on his cheeks.

“Sam, we don’t have time,” Dean groans, but he’s unbuckling his seat belt, reaching to slide his hand back under Sam’s skirt.

“Won’t take long,” Sam mumbles, undoing his own belt and leaning back, thighs spreading invitingly. “And I could still wear it after, right? Just for the ride?”

Fuck, Sam’s gonna kill him. Dean just nods and shoves the skirt up, gets a hand on Sam’s cock and watches as his little brother’s head falls back against the seat, hips lifting.

“Wait,” Sam gasps out, squirming out of Dean’s reach. “Dean, wait.”

With considerable effort, Dean pulls his hand back.

“Wanna do something for you this time.” Sam’s looking at him so earnest and sweet and eager and Dean can’t believe what he’s hearing.

“Dude, believe me, this does something for me. In a big way.”

“Please,” Sam asks, twisting in his seat to face Dean full on. Fuck, there go the puppy eyes. “C’mon Dean, let me do something just for you.”

“Alright,” Dean says. Like it’s a hardship. “What do you wanna do?”

“Anything.”

Anything. Anything Dean wants, right now. There’s no doubt in his mind that Sam is serious - that’s his serious face right there, eyes wide, mouth stiff like he’s trying to force Dean to believe him, to understand. Dean wonders if this is another thing Sam needs, to give Dean this.

He could fuck Sam, right here in the car; there’s lube in the duffel and Sam would let him. Jesus, this is fucking with Dean’s head.

Dean pops the button on his jeans, unzips and pulls his cock out with a sigh of relief. He gives himself one stroke, base to tip, just to take the edge off and watches as Sam’s eyes widen, throat bobbing as he swallows before moving forward, knees sliding up onto the seat. He’s leaning in like he thinks Dean wants a blowjob - and yeah, the thought of Sam on his knees with that goddamn skirt up around his waist, pink lips wrapped around Dean’s cock while Dean gets his hands in Sam’s hair and fucks up into his mouth, well, it’s a good image - but that’s not what Dean’s asking for.

He’s been thinking about how soft those panties are since he felt them stretched over Sam’s hard on, and he’s pretty sure he knows exactly what he wants from Sam - something Sam mentioned last time they did this. Dean reaches over and gets a hand on each of Sam’s hips, lifts him up and settles him on his lap with a smile at Sam’s little yelp of surprise.

This is so different from last time, he thinks as he grinds Sam down against his cock, silky-smooth fabric slipping over him, drawing a moan from Sam and a rough “fuck” from Dean. Last time they didn’t touch until it was over, it was all hot, sparking tension and murmured filth. This time, Dean can get his hands on Sam, dig his fingertips in and shove his own hips up and feel Sam shudder against him, little panting gasps and whimpers against his cheek.

It’s so easy to move Sam’s hips, to slide him up and down against Dean’s cock just the way he wants while Sam moans and arches in Dean’s hold, thighs spread over Dean’s and hands clamped on Dean’s shoulders. Dean remembers what Sam said last time though, about Dean making Sam ride him, so he loosens his grip on Sam’s hips and lets his hands splay loose and open over Sam’s ass, tucked under the rucked-up skirt.

“Ride me,” Dean grits out, and Sam’s hips give an involuntary jerk before he starts to roll them, pushing his cock against Dean’s, sliding them together in quick, smooth thrusts.

“Good boy, you’re so good, fuck Sammy you‘re so pretty like this.” It’s true - Sam’s face is flushed, flustered, he’s biting his lips and keeping his slitted eyes on Dean as he moves his body over him. His panties are getting wet with precome, both Sam and Dean’s, and they’re clinging to his cock perfectly, stretched tight over him, letting Dean feel every twitch and flex.

“Gonna come Sammy? Gonna come in your panties, get them all wet for me? I’m gonna make you wear ‘em, make you wear your come all day long.”

Sam’s starting to tremble, hands tightening on Dean’s shoulders, eyes screwing shut with pleasure as his hips give a few more erratic shoves before going still, tense, his whole body tightening with the force of his orgasm. Dean was already close, riding the hard edge of too much and not enough and the way Sam looks, feels when he comes has Dean desperately gripping his ass and grinding him down, Dean’s own hips coming up to shove against Sam as Dean comes, Sam still shuddering with aftershocks.

Sam pulls away before Dean’s ready but he gets that the kid is probably painfully oversensitive, so he drags out the last few waves of pleasure with a hand around his cock before reaching over and rubbing the last bit of come into Sam’s already soaked panties.

Sam glares down at him like those extra drops offended him but he curls himself against Dean’s side, letting his skirt fall over his thighs, hiding the mess underneath. Dean knows he’ll have to change into pants before they meet Dad for lunch - fuck, they’re gonna have to gun it to catch up - but for now he lets Sam come down pressed into his side.

“That was... really good,” Dean says, settling Sam into the passenger seat and buckling him up. Sam’s still in a daze - It’s like he’s a little high, like doing this with Dean takes him somewhere else and Dean has to wait for him to come back. “Sam?”

Sam blinks up at him before murmuring “Yeah Dean,” like he’s half asleep.

“You know that stuff we did last time - you know I liked that, right? You know it wasn’t just for you?”

Sam stares at him for a couple seconds before nodding slowly.

“Yeah, I’m getting that.”

“Good.” Dean starts the car, pulls back onto the main road. “Gonna have to change out of that skirt soon.”

Sam mumbles something like “I know.”

“Keep the panties on. Wanna know you’re wearing our come under your jeans.”

Sam gives a full body shiver at the words, eyes snapping open and cheeks darkening, but he nods and shifts in his seat, skirt already starting to tent where he’s getting hard.

Fuck, this thing might actually kill Dean.

 


End file.
